Things can't get any worse
by Ummm.Okay I got nuthin
Summary: This idea just came to me and I had to write it down. This is going to be a bunch of drabbles and oneshots written based off of requests. They can be about absolutely anything. I can do two-shots as well as multi chapter ones. No ships though! Oh and an OC can also be included, if requested.
1. Chapter 1-Things can't get worse

The loud rumbling of the engine cut through the silence of that dark night like a sharp knife, the headlights showing brightly again the blackness surrounding it. The 67' Chevy Impala was a black beauty, the only one of its kind, and I can say this with complete confidence. For although there may have been plenty of 1967 Chevy Impalas manufactured back then, none of them had been through anything that even came close to what this car had been through. None of them could boast of having travelled with two children who had turned out to be heroes.

It was all of a sudden that the boys found themselves in utter and complete darkness. The soothing sounds of the engine abruptly stopped and there was silence again.

"Well," The eldest of both the boys said, adding a side grin to his features as he continued, "looking on the bright side, at least now things can't get any worse."

Just a second later, the brothers start hearing the sounds of rain falling on the roof followed by an obvious bitchface from the younger brother directed towards the older one.

"Oh crap!" Dean mumbled under his breath.

"Somebody help us!" Sam cried out loud, "I'm stuck in the car with my obnoxious big brother!"

"No you are….I am _not_ obnoxious!" Dean exclaimed, turning around to face Sam.

Sam only glared at Dean in response.

"Shut up!" Dean said, "I'm adorable!"

 _Help!_

* * *

 ** _A/N: This first one was a little short, I admit, but it was just me testing my drabble-writing skills. Anyways, one-shot/drabble requests are welcome. Seriously, send requests! Alright I hope you enjoyed this little drabble. Next one will be coming soon enough..._**


	2. Chapter 2-I'm proud of us

A/N: This one is as per Panda13216's request-a short one shot of Sam taking care of whump!Cas and whump!Dean.

I thought a lot about when to set this one and decided to set it in Season 5 Episode 3-Free to be you and me.

* * *

Sam opened the door to his motel room, still thinking about Lindsay and the dinner he'd just had with her. But it didn't take too long for his instincts to kick in. He wasn't alone; there was somebody in here with him.

Sam pointed his gun at the intruder and turned on the lights. He was so shocked to see Dean and Castiel that he almost dropped his gun.

"What are you guys doing over here?" He asked in a shocked tone and noticed a little too late that his brother and the angel weren't exactly in the best of conditions.

"Heya Sammy!" Dean said, clearly drunk. He stood up and stumbled a little bit when he walked towards Sam.

"Hey, whoa, whoa, whoa. Dean, take it easy," Sam said as he sat Dean down again.

"Hello Sam," the angel greeted, also sounding a little out of it.

"Hey Cas," Sam replied, "What happened to you guys?"

Before Castiel could even try to reply, Dean put a hand on Sam's shoulder and patted it, "Sammy, have I ever told you that you are the best little brother anyone could ever have?"

Even though Sam knew that Dean was drunk and was probably saying the most random things, he still felt tears welling up in his eyes. "No Dean you haven't." And _I haven't been much of a good brother to you lately either._

"Well, I'm telling you now," Dean said, putting both his arms around Sam in a hug, "You're awesome!"

Sam could feel his shoulders tensing as he took Dean to his bed. Dean fell onto the bed heavily and closed his eyes.

"How did you guys get hurt?" Sam asked the angel who was still sitting on the edge of the couch, looking at the wall opposite him.

"The security guards beat us up," Cas muttered.

"The guards…why?" Sam looked at Cas, straight up confused.

"Because I told Chastity that her father did not run away because of her. It was not her fault." Castiel spoke in a matter-of-factly way.

"What?!" Sam had no idea what the angel was saying, which meant that the angel had to have been just as drunk as Dean was. "You know what Cas, we'll talk about this tomorrow. I think you need to get some rest right now."

"You are right," the angel replied as he got comfortable on the couch. Sam noticed the blood on his trench coat and on Dean's flannel but figured that the angel must've healed them both.

He shook his head as he saw Castiel closing his eyes, and got ready to sleep on the floor. Just then, he heard Dean calling out his name and felt his heart ripping to pieces. He'd never thought that he'd get to see Dean again, let alone hear him calling out his name. So he went near Dean's bed, "What is it Dean?"

"Have I ever told you how proud I am of us?" Dean asked the one question, said the one thing Sam had thought he'd never say again.

"No Dean you haven't."

* * *

Years later when Metatron slid the angel blade into Dean's chest with the Mark of Cain on his arm, he still remembered the events of that night and realised something. Castiel could have zapped them to any place at all, but he had specifically gone to Sam's apartment because he knew how stubborn the Winchesters were.

So as he spent his last few moments with his brother, he remembered that night and said, "I'm proud of us."

* * *

A/N: In my defence, I started off doing exactly what was mentioned in the request but I guess I went a little off the track. So Panda13216 does this count or should I do it properly in the next chapter?


	3. Chapter 3-Squeaky new shoes

"Squeak." It was so quiet at first that Sam wasn't sure that he'd heard it at all. Closing his eyes again, he turned to the side and put his hands under his pillow.

"SQUEAK!" The noise was loud enough for Sam to sit up straight in his bed. He slipped out of the covers quietly and crept towards his door, hoping that it was a rat that was making this noise.

"Squeak squeak squeeee-squueee squeeaaakkk."

"DEAN!"

At hearing Sam bellowing his name out loud, Dean stopped trying to slide across the floor in his new shoes and looked at Sam like a child who'd done something wrong.

"What the hell are you doing?" Sam asked, scrubbing his face down tiredly. It was 2am. Trust Dean to still be awake at this time of the night.

"I'm trying out my new shoes," Dean told his brother enthusiastically.

They'd passed a shoe store while coming back from the grocery store and Dean had used his extra pool money to get himself some brand new shoes. He'd asked Sam if he'd wanted some new shoes too, but Sammy had shrugged and said that there was nothing wrong with the shoes that he wore right now.

"Why?" Sam asked his brother, blinking his eyes furiously as his eyelids got heavy.

"Because….," Dean started off, moving his feet from side to side. It was because Dean would never admit it but he had secretly wanted to try out these new shoes ever since he'd bought them. He'd decided that he'd wait until he was alone to try them out but he really couldn't delay it any longer.

Sam suddenly noticed the joyful expression on his brother's face and realised the same thing. It was very rarely that Dean got to buy something for himself and it was only when Sam had told Dean to get himself the new shoes that he'd actually decided to buy them for himself. "They are pretty cool, though aren't they?" Sam asked, smiling when he saw his brother nodding excitedly.

"Yeah," Dean said clearing his throat, "and I got you a pair too." He went to his room and retrieved a pair of shoes which, Sam had to admit were, were pretty awesome.

As Sam stepped forward and took the shoes, trying them on, he also had to admit that they were pretty comfortable and fit him perfectly. In fact, he definitely liked them more than the shoes he wore now.

"You like them?" Dean asked, recognising the look on his brother's face.

"Yeah," Sam answered with a smile that showed his teeth, dimples deepening, "Yeah. They're great! Thanks, Dean."

Dean flashed Sam a quick smile before ruffling his hair and shook own head as he headed towards his own bedroom, glad to know that he'd made the right call when he'd impulsively decided to buy his brother a new pair of shoes too.

Just as Dean was getting comfortable in his own bed, sighing as he wrapped the bed sheet around himself-

"Squeeaaak squeeee-squee-squueee."

"Dammit Sammy!"


	4. Chapter 4-Let it go

"Why don't you two watch TV while I go get us something to eat?" Dean had told Cas and Sam as he'd put on his leather jacket, ready to go out into the cold night.

He'd regretted his decision the moment he'd heard that horrible song coming out of his brother's mouth.

* * *

"Let it go, let it go," Sam sang and paused just as Dean froze outside his room, "la la la la la la la." Sam sang the rest of the song humming the tune to the now forgotten words.

 _What the hell?_

Dean burst into Sam's room and Sam almost jumped up in shock, "What the hell, Dean?"

"That's what I'd like to ask you, genius!" Dean exclaimed, "What weird song are you singin'?"

"Oh," Sam seemed to be embarrassed to be caught in the act and scratched the back of his head, "it's just something Cas and I were watching on TV."

"Course it is," Dean muttered with a sigh, shaking his head as he walked out of Sam's room.

* * *

The next incident happened when Dean had gone into the bathroom to do his...ahem...daily business. He was just thinking about Cas in general and wondering what the angel was doing. He didn't know what happened next but he heard a fluttering of wings and the next thing he knew, the trench-coated angel was standing outside the bathroom singing the same damn song.

"Let it go! Leet it goooo!" Cas sang because for some reason, since he and Sam had watched that animated movie, he just couldn't get that song out of his head.

"Dammit Cas!" Dean grumbled as he emerged from the bathroom, "The hell is wrong with you people. First Sam sings this god awful song and now you."

* * *

The next time was during one of their prank wars. Dean couldn't even remember who had started it off or how exactly it had started off, he just knew that Sam had never let him hear the end of it.

He still hadn't forgiven Sam for it either and it had taken him a whole week of reminding himself of a good enough reason to not kill his brother, because after what Sam had done, Dean really had run out of reasons. Sam, having had enough sense, hadn't even dared to show his face to Dean for the first fourty-eight hours and had kept his distance even after that.

Dean had already played a wicked prank on Sam and was alert enough afterwards. He stayed on his heels the whole day, waiting for Sam's turn to pull the prank on him. So he was completely tired by night time, and completely oblivious to the fact that Sam had planned something very special for him.

He only heard soft whispers as he started to wake up the next morning.

"So what do you think Cas?" That was his brother, Sam's voice.

"I don't think we should be doing this, Sam. Dean will not be happy," Cas said and Dean could practically hear the frown in his voice.

"I know, man. Dean's gonna kill me but it's totally gonna be worth it," Sam said and Dean swore he saw a flash and then heard a click.

"He does look exactly like her, though," Cas said, just as Dean opened his eyes.

"The hell are you two doin' in my room?" Dean asked as both Cas and Sam froze.

"Hello Dean," Castiel greeted his friend, but Dean wasn't looking at him anymore. He was looking right past him, at a mirror.

"Son of a bitch!" Dean angrily exclaimed when he realised what Sam had done. The li'l bastard had put a blonde wig on him and taken pictures of it.

"Oh, come on Dean," Sam choked on his laughter managed to gasp out in between his breathes, "We just wanted to see how closely you resembled Elsa."

But Dean didn't hear what he was saying. He could only see red. "Sammy, I'm gonna kill you," he exclaimed just as Cas disappeared and Sam ran out of his room.

Dean sprinted after Sam, reminding himself to put deal with Cas after he was done with Sam.

* * *

So there he was right now-sitting down, getting ready to watch Frozen with both Sam and Cas sitting on opposite sides of him. He suspected, though that the reason for them both sitting so close to him had less to do with the fact that the bed was small and more because they wanted to make sure Dean didn't escape while watching the movie.

After the movie was over and Dean had teased both his brother and the angel plenty about the movie, he had to admit that the song was kind of catchy. So when he was getting a shower the next day, he couldn't help but hum that song under his breath.

Also, now that he thought about it, maybe when Sam was asleep at night Dean would pay him a visit and see just how closely _he_ resembled Princess Anna.


	5. Chapter 5-Things can't get worse II

Sam was stuck in a tiny bathroom stall in an abandoned house which was practically in the middle of nowhere. He was pretty sure that things couldn't get any worse, but did he say it out loud? No, he didn't because he knew that saying it out loud actually _did_ make things even worse. So he did what any sane person would do-he shut his trap and waited.

"Son of a bitch, Sammy. You mind getting your ass off of my face?" Dean asked him _really politely_ like his _'well-behaved'_ brother usually did.

Oh, had Sam mentioned that his brother was stuck in here with him?

He somehow inched away from his big brother and yelled out as Dean started shifting to a more comfortable position, where his little brother's ass wouldn't be anywhere near him. Dean froze when he heard Sam yelling, quickly giving the stall a once over before giving his brother a questioning look.

"You're stepping on my arm, Dean," Sam told him with a pained look on his face and Dean quickly pulled his leg away as Sam tried to shift to a much better position, too.

After a couple of moments of silence, Dean, being the restless jerk that he was, just had to open his trap and say, "Well, I guess now things can't really get any worse, eh Sammy."

Dean's grin faded as he saw the look on Sam's face. He looked like he was resisting the urge to punch Dean. It took few moments for Dean to understand what he had just done. As he remembered what had happened the last time that he had said those words, he realised his mistake. Yup, he had just sealed his brother's and his own fate.

Sam was practically waiting for it to happen and couldn't stop the sinking feeling that he got his stomach because _Dean had said it dammit!_ His stupid brother had said it out loud and it was as if God took Dean's words as a personal challenge because the very next second, they heard door unlocking and slowly opening.

Now normal people would've taken this as a good sign and sighed in relief, but the Winchesters were not normal people. They had been working a case over here and the evil spirit of Meredith Ross had been the one to trap them in the tiny stall in the first place.

Both the brothers remained frozen in their places, not daring to go out, not even daring to _move_.But just as the brothers were finally starting to get the courage to take the first step towards the door, the ghost appeared right in front of them looking as scary and frightening as ever.

"Die die die!" She chanted the words over and over again as her lips widened into a creepy smile at the very thought of the things she was going to do to them.

Sam and Dean swallowed heavily and before anything else could happen, Sam slid his eyes over at Dean. "Dude, if we die, I think I'll give Gabriel a visit so that, y'know, he can kill you over and over again in like a hundred different ways!"

Dean huffed and shrugged his shoulders as if saying 'whatever' and winced as he faced the angry spirit.

Had Sam mentioned that they were both weapon less?


End file.
